Siesta Key Vacation Rentals

Find Weekly, Monthly and Annual Rentals
in Siesta Key and Sarasota FL

Monthly Rentals

Beautiful 5th floor condo with stunning panoramic Gulf views from the wall of windows spanning the entire width of the unit. Office area w/2 desks. Private beach, bay access, gated community. Sleeps 4

Beautiful 5th floor condo with private beach and stunning water views from every room! Spacious, open-concept 2 bedroom, gourmet kitchen, large lanai. Sleeps 4 w/king beds in both bedrooms.

Spacious 3 Bedroom, 2.5 bath Gulf Front with gorgeous water views and private beach. Updated gourmet kitchen, large screened lanai. Located on the quieter Southern end of Siesta Key. Heated pool & bay access. Sleeps 6

Spacious waterfront condo overlooking Turtle Beach Inlet with private beach and bay access. Relax on the large enclosed lanai while watching boats, kayaks & paddle boarders float by on the bay. Sleeps 4

Beautifully remodeled townhouse with 2 floors of living space, 2 lanais and a porch. Spacious unit with views of tropical landscaping and mature trees. Large BBQ/Picnic area and fishing piers on the bay. Watch for dolphin in the bay waters! Sleeps 7

Great location, 2 blocks to the beach! Walk to, shopping, restaurants, and night time entertainment. Recently remodeled with updated kitchen & baths. New bed in master, new queen bed in guest bdrm. Heated pool. 2 bdrm/2 bath, sleeps 5

Relax and enjoy your own piece of paradise at this luxurious Casarina condominium on beautiful Siesta Key! Casarina complex is located in a very private setting just south of the public beach. Enjoy the lush tropical garden view from your lanai, a w

2 bdrm, 2 bath condo with screened lanai located at Bay Oaks resort on Siesta Key. Beautiful bayside waterfront picnic area where dolphins can be seen passing by. 2 large fishing piers w/fish cleaning station. Sleeps 4

Gorgeous 2 bedroom Siesta Key waterfront condo right on the beach with spectacular views from every room! Large 7th floor unit at Fisherman's Haven on the quieter southern end of the island. Sleeps 6

Weekly Rentals

Spacious 2 bedroom, 3rd floor condo at The Anchorage with private deeded beach access to Crescent Beach. Great location, walk to shopping & restaurants. New furnishings, many amenities. Sleeps 6

Charming 2 bdrm in great location just 2 blocks to the Beach. 5 minute walk to many shopping & dining options. Easy access on & off the island. Heated pool. Sleeps 4

2 bdrm, 2 bath condo with screened lanai located at Bay Oaks resort on Siesta Key. Beautiful bayside waterfront picnic area where dolphins can be seen passing by. 2 large fishing piers w/fish cleaning station. Sleeps 4

First Time Renting and Everything is NEW! This custom home is being offered for rent for the first time and everything inside is new including all furniture, beds, linens, dishes, TV’s etc. Private courtyard with heated pool. Sleeps 13!

Gorgeous 3 bedroom, 2 story Siesta Key home with private pool, close to the north bridge for easy access on and off the island. Full size washer & dryer. 2 patio areas. Bicycles, beach toys, and many more extras provided. Sleeps 8.

Gorgeous waterfront condo on Blind Pass Lagoon in Siesta Key just a short 3-5 minute walk from Turtle Beach. Relax and enjoy peaceful surroundings, fish from the docks, take a dip in the pool. Sleeps 6

Siesta Key vacation rental at Cozy Cove on the quieter Southern end of the island. Located waterfront on Blind Pass Lagoon with Docks provided. 5 minute walk to Turtle Beach, restaurants & entertainment. 2 bedroom, sleeps 4

2 bedroom condo located on world famous Crescent Beach in Siesta Key! Private beach area with loungers provided. Enjoy the tiki hut BBQ/picnic area on the beach. Nicely furnished and close to dining, shopping, and night time entertainment.

Stunning views of everything from the Gulf of Mexico & Siesta Key Beach to fantastic sunsets & downtown Sarasota. Located just across from world-famous Siesta Key Beach. Walk to Siesta Key Village by sidewalk or beach. Sleeps 6

Annual Rentals

Unfurnished 3 Bedroom, 3 bath private villa with new paint throughout, new carpet in bedrooms, new flooring in living room, new AC. Florida Room overlooks a lush tree lined greenbelt walking path, separating your home from the other Villas.

Charming & bright two bedroom, one bath condo located in the recently renovated Bay Oaks complex on Siesta Key. This is a furnished, turn-key unit with linens and a fully stocked kitchen (dishes, pots & pans, etc.) provided. Located on the ground flo


6623 Midnight Pass Road Siesta Key, FL 34242


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